
Holiday rentals in Siena
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Siena
Guests agree: these stays are highly rated for location, cleanliness and more.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Piazza del Campo Honeymoon Suite: romantic gateway
The 800-year-old Palazzo Accarigi, a Palazzo-Tower overlooking Piazza del Campo, offers a dreamy suite for Honeymoons and Anniversaries. As inside a fairy-tale, you will sleep in a princely baldaquin with a magnificent view of Piazza del Campo, while the highest quality noise-reducing windows will ensure you the quietest stay This suite offers a private and safe place to live the most authentic Tuscan lifestyle: plan to stay more days, use this flat as a base to explore Siena province.

Monteriggioni Castello, holiday house in Tuscany
Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Casa Fusari - Apartment next to the Duomo
! Please check the house rules before booking ! Completely renovated apartment with fine finishes located in a building of 1746, one minute walk from Piazza del Duomo and two minutes from Piazza del Campo. Strategic position in the heart of the historic center, very convenient raised ground floor from which you can see part of the Duomo, next to the apartment you will find two great restaurants. A few steps away you will also find the escalator to the parking lot Santa Caterina.

Green – The meadows in Tuscany
Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

"Red Rose" apartment with view of Siena.
Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

"La Lambarda" tower Suite
In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.
Popular amenities for Siena holiday rentals
Other great holiday rentals in Siena

The Arches of Corsanello | Apt "Siena" x 3

Villa di Geggiano – Guesthouse

Peaceful location ~ Great views ~ Garden ~ Parking

Wine Loft in the vineyards

The twigs

Cipressini 2 - pool and amazing views

Pociano.1863 The Horizon Suite

Palazzo Trapani Luxury Residence
Destinations to explore
- Rentals with a fireplace Siena
- Tent rentals Siena
- Townhouse rentals Siena
- Castle rentals Siena
- Apartment rentals Siena
- Smoking-friendly rentals Siena
- Villa rentals Siena
- Tiny house rentals Siena
- Hotel rentals Siena
- Rentals with a cinema Siena
- Luxury rentals Siena
- Family-friendly rentals Siena
- Flat rentals Siena
- Cottage rentals Siena
- Rentals with an EV charger Siena
- Rentals with an accessible-height bed Siena
- Rentals with beach access Siena
- Rentals with pools Siena
- Boutique hotel rentals Siena
- Private suite rentals Siena
- Serviced apartment rentals Siena
- Rentals with a firepit Siena
- Rentals with a patio Siena
- House rentals Siena
- Rentals with outdoor seating Siena
- Rentals with a washing machine and dryer Siena
- Rentals with a sauna Siena
- Fitness-friendly rentals Siena
- Holiday home rentals Siena
- Rentals with a balcony Siena
- Nature eco lodge rentals Siena
- Rentals with a hot tub Siena
- Farm stay rentals Siena
- Guest house rentals Siena
- Loft rentals Siena
- Rentals with breakfast Siena
- Pet-friendly rentals Siena
- Waterfront rentals Siena
- Barn rentals Siena
- Bed and breakfasts Siena
- Rentals with lake access Siena
- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Kite Beach Fiumara
- The Boboli Gardens
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Cala Di Forno
- Medici Chapels
- Things to do Siena
- Sightseeing Siena
- Nature and outdoors Siena
- Art and culture Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Things to do Italy
- Sports activities Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sightseeing Italy
- Entertainment Italy
- Wellness Italy
- Tours Italy
- Food and drink Italy